Cheap Flights from Milan to Chicago, IL from $418

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On Cheapflightsplus.com you will find 1 direct and 999 connecting flights from Milan to Chicago. You can compare airfare deals from 39 airlines and multiple travel sites from $418, book and save on cheap plane tickets and last minute offers. Also check out MIL-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Milan to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $418 (one-way), $717 (round-trip).

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Best Flights from Milan to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Milan to Chicago with the lowest price of $418. The fastest direct flight takes 10h 5m and the fastest connecting – 11h 45m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $904 Find flight	15:05 Milan Malpensa	18:10 Chicago O'Hare International	10h 5m	United Airlines	UA415
from $578 Find flight	17:45 Milan Malpensa	15:30+1 день Chicago O'Hare International	28h 45m layover 16h 15m - Lisbon	TAP Portugal	TP827 TP243
from $583 Find flight	11:55 Milan Malpensa	22:55 Chicago O'Hare International	18h 0m layover 6h 25m - New York	Neos	NO787 NK225
from $615 Find flight	19:55 Milan Malpensa	10:50+1 день Chicago O'Hare International	21h 55m layover 9h 25m - Belgrade	Air Serbia	JU419 JU506
from $418 Find flight	13:15 Milan Malpensa	00:34+2 дня Chicago O'Hare International	42h 19m layover 5h 15m - Paris 24h 50m - Newark	EasyJet	U24544 N0301 NK329
from $423 Find flight	07:15 Milan Malpensa	20:08 Chicago Midway	19h 53m layover 4h 30m - Reykjavik 2h 9m - Baltimore	EasyJet	U23969 OG101 F93087
from $438 Find flight	21:05 Milan Malpensa	10:05+2 дня Chicago O'Hare International	44h 0m layover 21h 20m - Paris 10h 30m - New York	Transavia France	TO3949 N0301 NK779
from $438 Find flight	20:15 Milan Malpensa	10:05+2 дня Chicago O'Hare International	44h 50m layover 22h 15m - Paris 10h 30m - New York	Vueling	VY8431 N0301 NK779
from $439 Find flight	15:00 Milan Linate	00:34+2 дня Chicago O'Hare International	40h 34m layover 3h 0m - Rome 24h 25m - Newark	Alitalia	AZ2071 N0401 NK329
from $444 Find flight	09:40 Milan Malpensa	22:55 Chicago O'Hare International	20h 15m layover 2h 10m - London 5h 25m - New York	Wizz Air UK	W96305 Z0701 NK225
from $450 Find flight	13:30 Milan Malpensa	17:09+2 дня Chicago Midway	58h 39m layover 22h 5m - Reykjavik 23h 8m - Baltimore	Aero Services Executive	W46453 OG101 F93087
from $458 Find flight	18:35 Milan Malpensa	14:33+2 дня Chicago O'Hare International	50h 58m layover 16h 15m - London 19h 15m - Miami	Aero Services Executive	W46303 Z0723 NK396
from $460 Find flight	10:30 Milan Linate	08:51+1 день Chicago O'Hare International	29h 21m layover 3h 15m - Berlin 10h 20m - Miami	EasyJet	U25064 N0623 NK1838
from $469 Find flight	22:05 Milan Malpensa	14:33+2 дня Chicago O'Hare International	47h 28m layover 12h 55m - London 19h 15m - Miami	EasyJet	U22486 Z0723 NK396
from $470 Find flight	22:15 Milan Malpensa	10:17+2 дня Chicago O'Hare International	43h 2m layover 8h 5m - Bucharest 20h 11m - New York	Aero Services Executive	W43064 H4101 NK779
from $475 Find flight	22:15 Milan Malpensa	00:34+2 дня Chicago O'Hare International	33h 19m layover 8h 5m - Bucharest 10h 30m - Newark	Aero Services Executive	W43064 H4101 NK329

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 09, 2025

Flight Schedule Milan to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Milan to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
15:05 — 18:10	15:05 — 18:10 UA415 United Airlines Milan — Chicago	10h 5m	Find flight from$904
11:55 — 22:55	11:55 — 14:50 NO787 Neos Milan — New York 6h 25m stop 21:15 — 22:55 NK225 Spirit Airlines New York — Chicago	18h including layover	Find flight from$583
17:45 — 15:30 +1 day	17:45 — 19:40 TP827 TAP Portugal Milan — Lisbon 16h 15m stop 11:55 — 15:30 TP243 TAP Portugal Lisbon — Chicago	28h 45m including layover	Find flight from$578
06:40 — 08:51 +1 day	06:40 — 07:50 W46301 Aero Services Executive Milan — London 6h 10m stop 14:00 — 18:45 Z0723 Z0 London — Miami 11h 45m stop 06:30 — 08:51 NK1838 Spirit Airlines Miami — Chicago	33h 11m including layover	Find flight from$480
06:40 — 10:02 +1 day	06:25 — 07:35 W46301 Aero Services Executive Milan — London 6h 10m stop 14:00 — 18:30 Z0783 Z0 London — Orlando 13h 30m stop 11:56 — 13:54 F91457 Frontier Airlines Orlando — Chicago	34h 22m including layover	Find flight from$485
07:15 — 20:08	07:00 — 10:35 U23969 EasyJet Milan — Reykjavik 4h 30m stop 15:20 — 17:00 OG101 Air Onix Reykjavik — Baltimore 2h 9m stop 16:20 — 17:27 F93087 Frontier Airlines Baltimore — Chicago	19h 53m including layover	Find flight from$423
08:55 — 10:05 +1 day	08:55 — 10:25 VY8433 Vueling Milan — Paris 8h 15m stop 18:40 — 21:00 BF720 Bluebird Cargo Paris — New York 11h 35m stop 08:35 — 10:05 NK779 Spirit Airlines New York — Chicago	32h 10m including layover	Find flight from$509
08:55 — 13:44 +1 day	08:55 — 10:25 VY8433 Vueling Milan — Paris 8h 15m stop 18:40 — 21:00 BF720 Bluebird Cargo Paris — Newark 15h 8m stop 12:08 — 13:44 NK329 Spirit Airlines Newark — Chicago	35h 49m including layover	Find flight from$545
09:40 — 22:55	09:40 — 10:50 W96305 Wizz Air UK Milan — London 2h 10m stop 13:00 — 15:50 Z0701 Z0 London — New York 5h 25m stop 21:15 — 22:55 NK225 Spirit Airlines New York — Chicago	20h 15m including layover	Find flight from$444
09:40 — 11:02 +1 day	09:40 — 10:50 W96305 Wizz Air UK Milan — London 2h 10m stop 13:00 — 15:50 Z0701 Z0 London — Newark 17h 36m stop 09:26 — 11:02 NK209 Spirit Airlines Newark — Chicago	32h 22m including layover	Find flight from$484
10:30 — 08:51 +1 day	10:30 — 12:15 U25064 EasyJet Milan — Berlin 3h 15m stop 15:30 — 20:10 N0623 N0 Berlin — Miami 10h 20m stop 06:30 — 08:51 NK1838 Spirit Airlines Miami — Chicago	29h 21m including layover	Find flight from$460
10:55 — 10:17 +1 day	10:55 — 12:35 W46339 Aero Services Executive Milan — Paris 6h 5m stop 18:40 — 21:00 BF720 Bluebird Cargo Paris — New York 11h 36m stop 08:36 — 10:17 NK779 Spirit Airlines New York — Chicago	30h 22m including layover	Find flight from$478
11:45 — 22:52 +1 day	11:45 — 13:15 U23807 EasyJet Milan — Paris 5h 25m stop 18:40 — 21:00 BF720 Bluebird Cargo Paris — Newark 24h 15m stop 21:15 — 22:52 NK329 Spirit Airlines Newark — Chicago	42h 7m including layover	Find flight from$533
13:15 — 00:34 +2 days	13:15 — 14:45 U24544 EasyJet Milan — Paris 5h 15m stop 20:00 — 22:05 N0301 N0 Paris — Newark 24h 50m stop 22:55 — 00:34 NK329 Spirit Airlines Newark — Chicago	42h 19m including layover	Find flight from$418
13:30 — 17:09 +2 days	13:30 — 17:15 W46453 Aero Services Executive Milan — Reykjavik 22h 5m stop 15:20 — 17:00 OG101 Air Onix Reykjavik — Baltimore 23h 8m stop 16:08 — 17:09 F93087 Frontier Airlines Baltimore — Chicago	58h 39m including layover	Find flight from$450
15:00 — 00:34 +2 days	15:00 — 16:10 AZ2071 Alitalia Milan — Rome 3h stop 19:10 — 22:30 N0401 N0 Rome — Newark 24h 25m stop 22:55 — 00:34 NK329 Spirit Airlines Newark — Chicago	40h 34m including layover	Find flight from$439
15:00 — 10:17 +1 day	15:00 — 16:10 AZ2071 Alitalia Milan — Rome 3h stop 19:10 — 22:30 N0401 N0 Rome — New York 10h 6m stop 08:36 — 10:17 NK779 Spirit Airlines New York — Chicago	26h 17m including layover	Find flight from$486
16:00 — 10:07 +1 day	16:00 — 17:10 AZ2059 Alitalia Milan — Rome 2h stop 19:10 — 22:30 N0401 N0 Rome — New York 10h 5m stop 08:36 — 10:17 NK779 Spirit Airlines New York — Chicago	25h 7m including layover	Find flight from$512
16:55 — 15:30 +1 day	16:55 — 18:30 VY6333 Vueling Milan — Barcelona 2h 40m stop 21:10 — 22:10 TP1039 TAP Portugal Barcelona — Lisbon 13h 45m stop 11:55 — 15:30 TP243 TAP Portugal Lisbon — Chicago	29h 35m including layover	Find flight from$547
18:35 — 14:33 +2 days	18:35 — 19:45 W46303 Aero Services Executive Milan — London 16h 15m stop 12:00 — 16:45 Z0723 Z0 London — Miami 19h 15m stop 12:00 — 14:33 NK396 Spirit Airlines Miami — Chicago	50h 58m including layover	Find flight from$458
18:35 — 11:02 +2 days	18:35 — 19:45 W46303 Aero Services Executive Milan — London 17h 15m stop 13:00 — 15:50 Z0701 Z0 London — Newark 17h 36m stop 09:26 — 11:02 NK209 Spirit Airlines Newark — Chicago	47h 27m including layover	Find flight from$475
19:10 — 11:02 +2 days	19:10 — 20:20 BA585 British Airways Milan — London 16h 40m stop 13:00 — 15:50 Z0701 Z0 London — Newark 17h 36m stop 09:26 — 11:02 NK209 Spirit Airlines Newark — Chicago	46h 52m including layover	Find flight from$542
20:15 — 10:05 +2 days	20:15 — 21:45 VY8431 Vueling Milan — Paris 22h 15m stop 20:00 — 22:05 N0301 N0 Paris — New York 10h 30m stop 08:35 — 10:05 NK779 Spirit Airlines New York — Chicago	44h 50m including layover	Find flight from$438
20:45 — 12:39 +2 days	20:45 — 22:15 VY8431 Vueling Milan — Paris 20h 25m stop 18:40 — 21:00 BF720 Bluebird Cargo Paris — New York 13h 59m stop 10:59 — 12:39 NK1681 Spirit Airlines New York — Chicago	46h 54m including layover	Find flight from$497
21:05 — 10:05 +2 days	21:05 — 22:40 TO3949 Transavia France Milan — Paris 21h 20m stop 20:00 — 22:05 N0301 N0 Paris — New York 10h 30m stop 08:35 — 10:05 NK779 Spirit Airlines New York — Chicago	44h including layover	Find flight from$438
21:55 — 12:39 +2 days	21:55 — 23:30 U24546 EasyJet Milan — Paris 19h 10m stop 18:40 — 21:00 BF720 Bluebird Cargo Paris — New York 13h 59m stop 10:59 — 12:39 NK1681 Spirit Airlines New York — Chicago	45h 44m including layover	Find flight from$475
22:05 — 14:33 +2 days	22:05 — 23:05 U22486 EasyJet Milan — London 12h 55m stop 12:00 — 16:45 Z0723 Z0 London — Miami 19h 15m stop 12:00 — 14:33 NK396 Spirit Airlines Miami — Chicago	47h 28m including layover	Find flight from$469
22:15 — 10:17 +2 days	22:15 — 01:30 W43064 Aero Services Executive Milan — Bucharest 8h 5m stop 09:35 — 12:25 H4101 Heli Securite Bucharest — New York 20h 11m stop 08:36 — 10:17 NK779 Spirit Airlines New York — Chicago	43h 2m including layover	Find flight from$470

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on May 9, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Milan to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milan and Chicago is 7289 miles. Time difference between the cities is 7h. Airplanes depart 03:15 to 23:40 from 4 Milan airports and arrive 03:15 to 23:40 to 7 Chicago airports. Average flight time is 10h 5m.

The fastest flight 10h 5m
Average flight time 10h 5m
The earliest flight 03:15
The latest flight 23:40
Distance 4530 ml

The cheapest months to travel to Chicago are december (from 418 $), february (from 423 $), november (from 438 $).

The most expensive months are january (from 444 $), november (from 438 $), february (from 423 $).

What is the lowest airfare Milan to Chicago?

The cheapest plane ticket found by our users is $418. This airfare is for economy class on one-way U24544 flight by EasyJet for December 12, 2024 which leaves Malpensa in Milan at 13:15 am and arrives at Chicago O'Hare International at 00:34.

Economy class

$418

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Business class

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First class

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Popular Airlines on the Route

The flight Milan — Chicago is served by 39 regular airlines and 8 low-cost airlines. Most of the flights on this route are operated by Neos - 11 departures per week at the price of from $ 583 . And the most expensive tickets are offered by United Airlines airline - from $ 1833.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA415 by United Airlines takes 10h 5m and the cheapest is U24544 by EasyJet for $904.

UA - United Airlines

from $904

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Connecting Flights

There are 999 flights with layovers on the route. The fastest connecting flight is UA9305 by United Airlines takes 11h 45m and the cheapest is U24544 by EasyJet for $418.

NO - Neos

from $583

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S4 - SATA International

from $660

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W9 - Wizz Air UK

from $444

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XZ - Ivoire Aero-Services

from $801

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VY - Vueling

from $438

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FI - Icelandair

from $899

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LO - LOT

from $1022

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BJ - Nouvelair Tunisie

from $760

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JU - Air Serbia

from $615

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LX - SWISS International Air Lines

from $672

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UA - United Airlines

from $677

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DY - Norwegian

from $602

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Airports

You can fly from Milan to Chicago from 4 airports (Linate, Malpensa, Milan Bergamo (Orio al Serio), Segrate).

Milan airports

Linate-LIN

from $439
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Malpensa-MXP

from $418
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Milan Bergamo (Orio al Serio)-BGY

from $541
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Segrate-SWK

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Milan by 39 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top International Destinations from Milan

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Milan — Miami

from $59

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Milan — Chicago

from $71

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Milan — Boston

from $79

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Milan — New York

from $72

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Milan — Los Angeles

from $60

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Milan — Atlanta

from $68

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Milan — Seattle

from $63

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Milan — Orlando

from $58

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Milan — Houston

from $56

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
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That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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